American stereotypes tell us that boys and men have a hard time talking about sensitive topics. It’s such a well-known cliché that Bud Light ran a series of commercials telling us it’s easy for a guy to say he loves his team or his beer, but it’s hard for him say “I love you” to either his girlfriend or his father.

John Gray published a half-dozen books telling us this happens because Men are From Mars, Women are From Venus. Whether or not you buy that—and I don’t—we all know the average American guy communicates differently than the average American girl. There are plenty of studies that demonstrate these kinds of group differences exist.

If you violate that trust and those moments of vulnerability by sharing what he’s told you with other people or you use what you now know in order to put him down, he won’t let you in again.

This doesn’t mean that dudes don’t have thoughts or feelings and it doesn’t mean they won’t share them. It does mean that the average guy isn’t going to spill his guts when you say “what’s up dude?” Perhaps you’re hoping to have a hear-to-heart with your father this holiday season or you need some ideas on how to reach out to your son.

Whatever your purpose, here are 5 strategies you can use to help create a more substantial conversation with a guy of almost any age. These suggestions come from Wayne V. Pawlowski who I met last week at the Center for Family Life Education’s National Sex Ed Conference.

Wayne is a Certified Sexuality Educator (via the American Association of Sexuality Educators, Counselors, and Therapists) and a Licensed Clinical Social Worker. He spent about 2 decades working as a sexuality educator for Planned Parenthood. There, he was often the “go-to” guy when it came to talking to teen boys and young men about their sexual behavior.

These strategies are effective for guys who are conforming to the “man box,” the stereotypical notions of what it means to be a man. The more stereotypical a guy is, the more useful these strategies are likely to be. And it doesn’t matter if you want to talk to a himbecause you’re a parent, a therapist, a sexuality educator like Wayne, or a friend.

1. Have something else to do/don’t make talking the primary activity. Guys rarely just sit and gab; they usually talk while doing some other activity. That activity can be almost anything—playing video games, watching sports, or fixing a car. And remember that just because he tunes into that other activity for a few seconds, or even a minute, it doesn’t mean he’s tuned out of the conversation. In those moments, he’s likely paying attention to what he’s feeling or what he’s going to say next.

2. Remember that he already knows everything, even if he doesn’t. American expectations tell us that boys and men are supposed to know it all and thus are not supposed to admit it when they don’t. That’s why guys don’t ask for directions. Asking “do you know about X” or “is there anything (else) you want to know” isn’t going to get you very far. You’ll probably have better luck starting with a topic where he is knowledgeable, then shifting to a topic where he may be less sure of himself. Questions like “what do you know about X” or “can you explain X to me” can also be helpful, as are follow up questions like “what about Y?”

Asking him to share his feelings includes an implicit request to risk losing his self-control.

3. Translate between thoughts, actions, and feelings. American cultural biases simultaneously highlight female emotionality and tell boys to avoid being girly. Through subtle and not-so-subtle encouragement from parents, siblings, friends, and teachers, boys learn to emphasize what they do and what they think over how they feel. For most boys and men, it’s easier to talk about what he’d think or do in a particular situation—real or hypothetical—than to talk about how he’d feel. Once he’s told you about his thoughts and actions and you’ve given them your attention, there’s a good chance he’ll respond honestly to a question like “…so it sounds like you were happy/sad/ excited/ angry/etc.” or even “how’d you feel when you were doing all that?”

4. Understand that feelings are dangerous to boys. From a young age, we teach boys and men that they should be in control. This applies to both self-control and control of a situation. Feelings aren’t controllable and thus present a real threat. Asking him to share his feelings includes an implicit request to risk losing his control.

5. Remember that peers are very important. We all get it that guys act differently when they’re with “the guys.” It’s the central premise of movies like “The Hangover.” This sometimes causes problems in guys’ one-on-one conversations with their male friends. For guys trying to live inside the man box, his male friends and the larger audience of “guys” are that much more important. No matter how much he thinks it’s the right thing to do or agree with you, he might not actually do it if it means he’ll lose some “man points.”

If you can follow these suggestions, then there’s a good chance you’ll have a different kind of conversation with that man than you’ve been having. It might even feel like you’re getting to see his true self, a self that you may have never seen.

The average guy isn’t going to spill his guts when you say “what’s up dude?”

There’s one more thing you need to remember. Whatever he’s told you, he’s done so in confidence. You worked within his boundaries and created a conversational space in which he felt safe and respected and thus earned his trust. Metaphorically, he’s taken off his armor. If you violate that trust and those moments of vulnerability by sharing what he’s told you with other people or you use what you now know in order to put him down, he won’t let you in again.